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Efficient regioselective aldol condensation of methyl ketones promoted by organoaluminum compounds, and its application to muscone synthesis

✍ Scribed by Jiro Tsuji; Toshiro Yamada; Mitsumasa Kaito; Tdakatsu Mandai


Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
245 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis


Regioselective aldol condensation of 2-octanone and 2-butanone at the methyl side proceeded in high yields using a system of dialkylaluminum phenoxide/tertiary amine. The intramolecular aldol condensation of 2,15hexadecanedione was carried out by the same system, especially di-i-butylaluminum phenoxide/pyridine, to give dehydromuscone in 65% yield. Its hydrogenation afforded muscone (3-methylcyclopentadecanone). 3) is called muscone and a famous naturally occurring fragrant compound. Among numerous synthetic methods for muscone so

3-Methylcyclopentadecanone (